Abstract
A series of 1-aryl-3-(cyclicamino)-prop-2-en-1-one analogs was synthesized from commercial acetophenones in 2 or 3 steps. Compound 6, (E)-3-(piperidinyl)-1-(2′-hydroxyphenyl)-prop-2-en-1-one, exhibited the unique shape and intensity of the Csp2NCH2peaks in the 1H and 13C NMR spectra. Variable temperature (VT) nuclear magnetic resonance (NMR) and X-ray diffraction (XRD) studies of 6 revealed that the piperidine ring has a lower energy barrier to rotation than the 5-membered pyrrolidine 9 due to the less effective π electron delocalization along the Csp2N bond.
Original language | English (US) |
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Pages (from-to) | 600-605 |
Number of pages | 6 |
Journal | Journal of Molecular Structure |
Volume | 1076 |
DOIs | |
State | Published - Nov 5 2014 |
Externally published | Yes |
Keywords
- Enaminones
- Flexible rotation
- VT-NMR
- X-ray diffraction
ASJC Scopus subject areas
- Spectroscopy
- Analytical Chemistry
- Inorganic Chemistry
- Organic Chemistry